Ansamycin: Difference between revisions

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[[File:Geldanamycin.svg|thumb|Structure of [[geldanamycin]], one of the benzoquinone ansamycins.]]
'''Ansamycins''' is a family of secondary metabolites that show [[antimicrobial]] activity against many [[Gram-positive]] and some [[Gram-negative]] bacteria and includes various compounds, among which: [[streptovaricins]] and [[rifamycins]].<ref>{{cite journal |author=Wehrli, W.; Staehelin, M. |journal=Bacteriol. Rev. |title=Actions of the rifamycins |volume=35 |issue=3 |pages=290290–309 |year=1971 |pmid=5001420 |pmc=378391}}</ref> In addition, these compounds demonstrate antiviral activity towards bacteriophages and [[poxviruses]].
They are named ansamycins (from the Latin '''ansa''', ''handle'') because of their unique structure, which comprises an aromatic moiety bridged by an aliphatic chain.<ref>{{cite journal |author=Prelog, V.; Oppolzer, W. |journal=Helv. Chim. Acta. |title=Rifamycins. 4. Ansamycins, a novel class of microbial metabolism products |volume=56 |pages=2279 |year=1973}}</ref> The main difference between various derivatives of ansamycins is the aromatic moiety, which can be a [[naphthalene]] ring or a [[naphthoquinone]] ring as in [[rifamycin]] and the [[naphthomycin]]s.<ref>{{cite journal |author=Balerna, M.; Keller-Schierlein, W.; Martius, C.; Wolf, H.; Zähner, H. |journal=Arch. Mikrobiol. |title=Metabolic products of microorganisms. 72. Naphthomycin, an antimetabolite of vitamin K |volume=65 |pages=303303–17 |year=1969 |pmid=4988744 |issue=4 |doi=10.1007/bf00412210}}</ref> Another variation comprises benzene or a benzoquinone ring system as in [[geldanamycin]] or [[ansamitocin]]. Ansamycins were first discovered in 1959 by Sensi et al. from ''[[Amycolatopsis]] mediterranei'', an [[actinomycete]].<ref>{{cite journal |author=Sensi, P.; Margalith, P.; Timbal, M. T. |journal=Ed. Sci. |title=Rifomycin, a new antibiotic; preliminary report |volume=14 |pages=146 |year=1959}}</ref>
Rifamycins are a subclass of ansamycins with high potency against mycobacteria. This resulted in their widespread use in the treatment of [[tuberculosis]], [[leprosy]], and AIDS-related mycobacterial infections.<ref>{{cite journal |author=Floss, H. G.; Yu, T. |journal=Curr. Opin. Chem. Biol. |title=Lessons from the rifamycin biosynthetic gene cluster |volume=3 |pages=592592–7 |year=1999 |doi=10.1016/S1367-5931(99)00014-9 |pmid=10508670 |issue=5}}</ref> Since then various analogues have been isolated from other prokaryotes.